IMPPAT Phytochemical information: 
Benzyl isoferulate
Benzyl isoferulate
Summary

SMILES: COc1ccc(cc1O)/C=C/C(=O)OCc1ccccc1
InChI: InChI=1S/C17H16O4/c1-20-16-9-7-13(11-15(16)18)8-10-17(19)21-12-14-5-3-2-4-6-14/h2-11,18H,12H2,1H3/b10-8+
InChIKey: URLDLSRJTIJNGH-CSKARUKUSA-N
DeepSMILES: COcccccc6O)))/C=C/C=O)OCcccccc6
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCCC1
Functional groups: cOC; cO; c/C=C/C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
benzyl isoferulate
External chemical identifiers:
CID:CID_14151009; SureChEMBL:SCHEMBL16155888
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Benzyl isoferulate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 284.31
Log P RDKit 3.16
Topological polar surface area (Å2) RDKit 55.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.12
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Benzyl isoferulate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.676596
Benzyl isoferulate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.67
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No